Key takeaways
- Vinny Lingham predicted in October 2024 that Saylor would damage Bitcoin more than FTX, with MSTR now down over 80%.
- The strategy holds $6.7 billion in convertible notes; Shin cites one analyst who estimates that covering early maturities requires selling up to 74,000 BTC or more.
- Lingham says STRC, which trades below $76, will never return to $100, and that the strategy’s cash flow is limited.
Lingham called it early
Praxos Capital co-founder Vinny Lingham, formerly known as “Oracle“, joined Laura Shin for an episode of the Unchained podcast broadcast on June 25, 2026. At the start of the interviewLingham was quick to walk back a prediction he had made two years earlier about the strategy, bitcoin treasury company formerly known as Microstrategy.
In October 2024, Lingham job a warning on X that Michael Saylor would ultimately do more damage to bitcoin that FTX. The prediction was mocked at the time. MicroStrategy was trading near its all-time high of $473.83. Since this week, MSTR has fallen more than 80% from that high, trading around $90.70.
“I posted a tweet in October 2024 saying that ultimately I thought Michael Saylor would do more damage to bitcoin than FTX,” Lingham explained during the interview with Shin.
He added:
“At the time, it was a very unpopular prediction. Now, 18 months later, people are starting to wonder if I was actually right.”
The “Saylor scheme”
Lingham doesn’t go so far as to call the strategy a Ponzi scheme, but he coined his own term for what Saylor built.
“He built an extremely complex capital structure consisting of debt and multiple layers of preferred securities,” Lingham argued. “I jokingly call it a ‘Saylor Plan.’ He issued STRC, STRD, STRK… and several others. When one offer no longer worked, he would simply introduce another.
STRC, one of the preferred share classes at the center of recent market concerns, closed today at $75.69, after falling below $74 earlier this week. Lingham doesn’t expect him to recover.
“I don’t believe STRC will ever go back to $100,” he said. “I’d bet he’ll never go back to au pair again.”
The end of chess
Strategy recently raised $335 million, selling 2.7 million shares of common stock and using about $300 million to increase its cash reserves to about $1.4 billion. This cash is expected to cover preferred dividend obligations for approximately 10 months. According to Lingham, the market responded by continuing to sell MSTR and STRC.
Lingham says the company’s recent decision to pay fortnightly dividends has made the situation worse. More frequent payment cycles mean management has less time to react when conditions deteriorate, and each cycle adds pressure to cash reserves.
He describes Saylor’s current position using a term from chess.
“Michael is now in what we call in chess zugzwang,” Lingham said. “Every move he has is a losing move. If he increases the dividend yield, he shortens his cash flow. If he issues more shares, he further dilutes common shareholders.”
The $6.7 trillion debt problem
During the discussion, Shin explained that Matt Walsh, founding partner of Castle Island Ventures, recently raised concerns on Strategy’s convertible notes, which total approximately $6.7 billion outstanding. Shin said the notes carry sales rights that allow holders to demand a cash refund at par if the notes are not converted or refinanced. Walsh estimated that covering the first three maturities until June 2028, at a bitcoin price around $60,700, around 74,000 would need to be sold BTC. To cover the entire program, approximately 111,000 bitcoin.
Lingham responded to Shin’s summary of Walsh’s X message and insisted that the market is already pricing in this risk.
“The strategy sold only 32 bitcoin and the market reacted negatively,” he said. “Imagine what would happen if the company ended up selling tens of thousands of products. bitcoin.”
The reflective loop in reverse
Lingham argues that the strategy’s aggressive accumulation created a self-reinforcing cycle that worked well as it gained momentum. The company purchased bitcoinwhich he says caused the price to rise, which increased the value of MSTR, which allowed him to issue more shares and buy more. bitcoin. He now says the cycle is reversed.
“Once Strategy ceases to be the largest buyer of bitcoinSelling pressure is starting to outweigh buying pressure,” he said. Liquidity disappears. The biggest source of demand has disappeared.
He added that the strategy’s mNAV, located around 1.06, is historically a level at which similar investment vehicles trade at a discount. He said a value closer to 0.90 would make more sense given the circumstances.
What comes next
Lingham told the Unchained podcast host that the healthiest outcome would be for Saylor to stop buying bitcoinstop issuing new shares, preserve your liquidity and wait for a resumption of the market cycle. He doesn’t expect this to happen.
“I don’t think he will admit that the strategy needs to change,” Lingham said. “I think pride plays a big role here.”
